Morpholine → HCID 23533840, compound

HRID 2414392Notes

Reaction equation

HRID 2414392 reaction equation
C([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:35]=[CH:36][CH:37]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:34])[C@H:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]#[N:15])=[O:6])C=C.N1CCOCC1>C1COCC1>[C:5]([C:7]1[CH:8]=[C:9]([CH:35]=[CH:36][CH:37]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:34])[C@H:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]#[N:15])([OH:6])=[O:4]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12148459HCID 12148459, compound

Product 1

HCID 23533840HCID 23533840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-[3-(allyloxycarbonyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-Nα-phenyl-L-phenylalaninamide (12.48 g, 25.11 mmol) in THF (500 mL), is added morpholine (21.9 mL, 251 mmol), and the solution is deoxygenated with bubbling N2 for 5 min. Pd(PPh3)4 is then added in one portion, and the solution is stirred at room temp. for 10 min. Solvent is evaporated, and the residue is dissolved in EtOAc (500 mL), and washed with 1 N HCl (500 mL), brine (200 mL), dried (MgSO4), evaporated and chromatographed (2%-10% MeOH/CH2Cl2) to yield N-[2-(3-carboxy-benzyloxy)-1(S)-cyanoethyl]-3-methyl-Nα-phenyl-L-phenylalaninamide, as a white solid; m.p. 135-137°.

Workup

  1. customthe solution is deoxygenated with bubbling N2 for 5 min
  2. additionPd(PPh3)4 is then added in one portion
  3. customSolvent is evaporated
  4. dissolutionthe residue is dissolved in EtOAc (500 mL)
  5. washwashed with 1 N HCl (500 mL), brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customchromatographed (2%-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3a1cc797174046f8b68c492ca78d093a
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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